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Arrange the following compounds in order...

Arrange the following compounds in order of their reactivity towards `S_N2` reaction
(i) `CH_3(CH_2)_3CH_2Br`
(ii) `(CH_3)_2CHCH_2CH_2Br`
(iii) `CH_(3)CH_(2)-overset(CH_(3))overset("| ")"CH"-CH_(2)Br`

A

`(i) gt (iii) gt (ii)`

B

`(ii) gt (iii) gt (i) `

C

`(iii) gt (i) gt (ii)`

D

`(ii) gt (i) gt (iii) `

Text Solution

AI Generated Solution

The correct Answer is:
To determine the order of reactivity of the given compounds towards the \( S_N2 \) reaction, we need to analyze the structure of each compound and their steric hindrance. The \( S_N2 \) mechanism favors less steric hindrance, allowing the nucleophile to attack the electrophilic carbon more easily. ### Step-by-Step Solution: 1. **Identify the Structures of the Compounds**: - (i) \( CH_3(CH_2)_3CH_2Br \): This is a primary alkyl bromide. - (ii) \( (CH_3)_2CHCH_2CH_2Br \): This is a secondary alkyl bromide. - (iii) \( CH_3CH_2-CH(CH_3)-CH_2Br \): This is also a secondary alkyl bromide. 2. **Determine the Type of Alkyl Halides**: - Primary alkyl halides (like compound (i)) have the least steric hindrance, making them more reactive in \( S_N2 \) reactions. - Secondary alkyl halides (like compounds (ii) and (iii)) have more steric hindrance compared to primary alkyl halides, which decreases their reactivity in \( S_N2 \) reactions. 3. **Rank the Reactivity**: - Since \( S_N2 \) reactions are favored by less steric hindrance, we can rank the compounds based on their structure: - Compound (i) \( CH_3(CH_2)_3CH_2Br \) (primary) will be the most reactive. - Between compounds (ii) and (iii), both are secondary, but we need to consider their structures: - Compound (ii) \( (CH_3)_2CHCH_2CH_2Br \) has a more branched structure compared to compound (iii) \( CH_3CH_2-CH(CH_3)-CH_2Br \), which makes (ii) slightly less reactive than (iii). - Therefore, the order of reactivity is: - (i) > (iii) > (ii) 4. **Final Order**: - The final order of reactivity towards \( S_N2 \) reaction is: - **(i) > (iii) > (ii)** ### Conclusion: The correct order of reactivity towards \( S_N2 \) reaction is: - **(i) \( CH_3(CH_2)_3CH_2Br \) > (iii) \( CH_3CH_2-CH(CH_3)-CH_2Br \) > (ii) \( (CH_3)_2CHCH_2CH_2Br \)**.
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